Tetracycline

Base Information

• Chemical Name: Tetracycline
• CAS No.: 60-54-8
• Molecular Formula: C22H24N2O8
• Molecular Weight: 444.441
• Hs Code.: 29413000
• Mol file: 60-54-8.mol

Synonyms:2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-(7CI,8CI);Abramycin;Achromycin;Acromicina;Actisite;Agromicina;Ambramicina;Arcanacycline;Bio-Tetra;Biocycline;Ciclibion;Cyclomycin;Deschlorobiomycin;Florocycline;Gammatet;Ibicyn;Kinciclina;Latycin;Medocycline;Mericycline;Micycline;NSC 108579;Omegamycin;Orlycycline;Panmycin;Resteclin;Retet;Robitet Robicaps;Tetra-Co;Tetra-Proter;Tetracycline;Tetralan;Tetralen;Tetramig;

Chemical Property of Tetracycline

Chemical Property:

• Appearance/Colour: Light yellow crystal
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 172-174 °C
• Refractive Index: 1.741
• Boiling Point: 790.622 °C at 760 mmHg
• PKA: pKa (50% aq DMF): 8.3, 10.2(at 25℃)
• Flash Point: 431.953 °C
• PSA: 181.62000
• Density: 1.644 g/cm³
• LogP: 0.48590
• Storage Temp.: 2-8°C
• Solubility.: 95% ethanol: soluble12.5mg/mL
• Water Solubility.: Limited solubility in water. Soluble in 1M HCl with heating.

Purity/Quality:

99.9% ^*data from raw suppliers

Tetracycline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 22-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: Tetracycline is an antibiotic that has been utilized in disease management situations in which SmR strains of E. amylovora or P. syringae already exist. However, tetracycline does not appear to be as effective as streptomycin in reducing blossom populations of E. amylovora (17). Additionally, strains of P. syringae with resistance to tetracycline have been isolated from pear orchards in Oregon and Washington (18), suggesting that resistance to this antibiotic will probably develop in orchards where it is applied.
• Uses: antibacterial, antiamebic, antirickettsial Tetracycline is a linear, tetracyclic, broad spectrum antibiotic first prepared chemically by dechlorination of chlortetracycline and subsequently isolated from several Streptomyces species. Tetracycline has broad spectrum antibacterial and antiprotozoan activity, and acts by binding to the 30S and 50S ribosomal subunits blocking protein synthesis. Tetracycline is a pigment and, like many pigments, is degraded by light, oxygen, trace metal ions and pH variations. The purity of tetracycline is often variable, with significant levels of degradation products. Tetracycline is a broad spectrum polyketide antibiotic. It is used clinically to treat bacterial infections such as Rocky Mountain spotted fever, typhus fever, tick fevers, Q fever, and Brill-Zinsser disease. It is used to treat upper respiratory infections and acne. It is used to study multidrug resistance as well as potential side effects such as acute pancreatitis. Antibiotic substance produced by Streptomyces spp. Antiamebic; antibacterial; antirickettsial
• Indications: Tetracycline is often the first antibiotic prescribed. It is the least expensive, has few side effects, and is well tolerated for longer periods of time. Tetracycline is effective in low doses because high concentrations are achieved within sebaceous follicles, especially when inflammation is present.
• Therapeutic Function: Antibacterial
• Clinical Use: Along with doxycycline it is one of the most commonly used tetracyclines.
• Drug interactions: Potentially hazardous interactions with other drugs Anticoagulants: possibly enhance anticoagulant effect of coumarins and phenindione. Oestrogens: possibly reduce contraceptive effects of oestrogens (risk probably small). Retinoids: possible increased risk of benign intracranial hypertension with retinoids - avoid concomitant use.

Technology Process of Tetracycline

There total 28 articles about Tetracycline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 62.0%

6-deoxy-6-hydroperoxy-5a,11a-dehydrotetracycline (102851-25-2) → TETRACYCLINE (60-54-8)

Guidance literature:

With hydrogen; platinum; In 1,4-dioxane; for 8h; under 2280 Torr;

DOI:10.1246/cl.2000.646

Reference yield:

C36H32N2O9 → TETRACYCLINE (60-54-8)

Guidance literature:

With hydrogen; palladium; In 1,4-dioxane; at 23 ℃; for 2.08333h; under 760.051 Torr;

Reference yield:

3,7-bis-benzyloxy-13-dimethylamino-11-hydroperoxy-4a-hydroxy-11-methyl-12a,13-dihydro-4aH,11H,12H-1-oxa-2-aza-cyclopenta[b]naphthacene-4,5,6-trione → TETRACYCLINE (60-54-8)

Guidance literature:

With hydrogen; palladium; In 1,4-dioxane; at 23 ℃; for 2h; under 760 Torr;

DOI:10.1021/ja052151d

upstream raw materials:

Chlortetracycline

6-deoxy-6-hydroperoxy-5a,11a-dehydrotetracycline

7-Methoxy-3-methylphthalide

anhydrotetracycline

Downstream raw materials:

tyrosine*tetracycline

Oxytetracycline

1,3-pentanediol

anhydrotetracycline

Refernces

• 1、 Herbst, Ehud,Lee, Arden,Tang, Yi,Snyder, Scott A.,Cornish, Virginia W.. "Heterologous Catalysis of the Final Steps of Tetracycline Biosynthesis by Saccharomyces cerevisiae". . p. 1425 - 1434. Retrieved 2021.
• 2、 -. "METHODS FOR ENGINEERING THERAPEUTICS AND USES THEREOF". . . Retrieved 2021/05/15.